Various N-acyl-acyloxy aromatic amines are known which can be used for the preparation of poly(ester-amide)s capable of forming an anisotropic melt phase and suitable for being formed into shaped articles such as moldings, fibers, and films, as disclosed, for example in U.S. Pat. Nos. 4,330,457; 4,339,375; 4,341,688; 4,351,918; and 4,355,132. However, none of these patents specifically discloses NODAN for this purpose.
U.S. Pat. No. 4,568,763, issued Feb. 4, 1986 to Davenport and Hilton, discloses the production of N-acyl-acyloxy aromatic amines by forming the oxime of a hydroxy aromatic ketone and subjecting the oxime to a Beckmann rearrangement in the presence of a carboxylic acid anhydride. The patent lists 2,6-naphthylene as a contemplated aromatic group.
Davenport and Linstid, U.S. Pat. No. 4,593,125, issued June 3, 1986, teaches the acylation of 2-substituted naphthalenes, e.g., 2-naphthol, with anhydrous hydrogen fluoride as catalyst, to obtain 6-substituted-2-naphthones such as 6-hydroxy-2-acetonaphthone (6,2-HAN).
Lewis, U.S. Pat. No. 2,833,825 shows the rearrangement of esters of phenolic compounds, e.g., beta-naphthol, to hydroxyaryl alkyl ketones using anhydrous hydrogen fluoride as catalyst. The working examples of this patent are limited to the rearrangement of esters of higher fatty acids.
Simons et al, Journal of the American Chemical Society, 62, 485 and 486 (1940) show the use of hydrogen fluoride as a condensing agent for various rearrangements and at page 486 show the Fries rearrangement of phenyl acetate to obtain p-hydroxyacetophenone.
Dann and Mylius in a dissertation included as part of a series of Reports from the Institute for Applied Chemistry of the University of Erlangen, received for publication on Jan. 7, 1954 and published in Annalen der Chemie 587 Band, pages 1 to 15, show the rearrangement of phenyl acetate in hydrogen fluoride to 4-hydroxyacetophenone. They also report the same reaction carried out by K. Weichert as described in Angewandte Chemie 56, 338 (1943). In addition, Dann and Mylius disclose the formation of hydroxy aromatic ketones from rearrangements in hydrogen fluoride of m-cresyl acetate, p-cresyl acetate, and guaiacol acetate.
Dann and Mylius also disclose the reaction of phenol and glacial acetic acid in the presence of hydrogen fluoride to produce 4-hydroxyacetophenone. This reaction may be conventionally characterized as a Friedel-Crafts acetylation of phenol with acetic acid as the acetylating agent.
Simons et al, Journal of the American Chemical Society, 61, 1795 and 1796 (1939) teach the acylation of aromatic compounds using hydrogen fluoride as a condensing agent and in Table 1 on page 1796 show the acetylation of phenol with acetic acid to produce p-hydroxyacetophenone.
Muessdoerffer and Niederprum in German Offenlengungschrift No. 2,616,986, published Oct. 27, 1977, disclose the acylation of phenols and substituted phenols with an acyl chloride in the presence of hydrogen fluoride to yield the 4-acyl derivative in high yield with high selectivity. The inventors disclose that 2-naphthol and 7-chloro-2-naphthol can be acylated according to their invention but do not teach any specific method for the acylation of the naphthol derivatives nor do they indicate what isomer or isomers are produced with such naphthol derivatives.
Auwers et al, Chemische Berichte, 58, 36-51 (1925) at page 41 show the Beckmann rearrangement of a large number of oximes of aromatic ketones most of which are substituted acetophenones. However, the only attempted rearrangement of the oxime of a hydroxy aromatic ketone was that of the oxime of o-hydroxyacetophenone, but no amine was formed, i.e., the attempted rearrangement was unsuccessful; see Auwers et al at page 41.
Ganboa et al, Synthetic Communications 13, 941-944 (1983) show the production of acetanilide from acetophenone by refluxing in a solution of hydroxylamine hydrochloride. There is, however, no suggestion of the synthesis of N-acyl acyloxy aromatic amines such as NODAN.
Pearson et al; Journal of the American Chemical Society 75, 5905-5908 (1953) disclose the formation of hydrazones from ketones by reaction with hydrazine hydrate and the rearrangement of the hydrazone to the amide by reaction with sodium nitrite and concentrated sulfuric acid. Specifically, on page 5907 Pearson et al show the rearrangement of p-hydroxyacetophenone hydrazone to p-hydroxyacetanilide.
Copending application Ser. No. 870,062 filed June 3, 1986, now U.S. Pat. No. 4,675,449, by Davenport discloses the preparation of 6-hydroxy-2-acetonaphthone (6,2-HAN) by the Fries rearrangement of 2-naphthyl acetate.